Investigation of π-π and ion-dipole interactions on 1-allyl-3-butylimidazolium ionic liquid-modified silica stationary phase in reversed-phase liquid chromatography

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1-Allyl-3-butylimidazolium bromide ionic liquid [AyBIm]Br was prepared and used for themodification of mercaptopropyl-functionalized silica through surface radical chain-transfer addition.The obtained ionic liquid-modified silica (SiImBr) was characterized by elemental analysis, infraredspectroscopy, NMR spectroscopy, and thermogravimetric analysis. The selective retentionbehaviours of polycyclic aromatic hydrocarbons (PAHs) including some positional isomers wereinvestigated using SiImBr as a stationary phase in reversed-phase liquid chromatography. Theresults showed that SiImBr presented multiple interactions including hydrophobic, π-π, andion-dipole interactions during the separation of PAHs and dipolar compounds. However, it isproposed that π-π and ion-dipole interactions play important roles in the separation of PAHs anddipolar compounds. These results indicate that the ionic liquid-modified silica stationary phase ispromising for future applications. A commercially available monomeric octadecylated silica (ODS)column and a custom-made poly(styrene)-grafted silica (Sil-Stn) column were used as references.
2010-08-06